EP4136064A1 - Synthesis of trifluoroacetyl iodide (tfai) from trifluoroacetyl chloride (tfac) and hydrogen iodide (hi) in a liquid phase reaction - Google Patents

Synthesis of trifluoroacetyl iodide (tfai) from trifluoroacetyl chloride (tfac) and hydrogen iodide (hi) in a liquid phase reaction

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Publication number
EP4136064A1
EP4136064A1 EP21784224.4A EP21784224A EP4136064A1 EP 4136064 A1 EP4136064 A1 EP 4136064A1 EP 21784224 A EP21784224 A EP 21784224A EP 4136064 A1 EP4136064 A1 EP 4136064A1
Authority
EP
European Patent Office
Prior art keywords
trifluoroacetyl
tfai
iodide
tfac
reactor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21784224.4A
Other languages
German (de)
French (fr)
Other versions
EP4136064A4 (en
Inventor
Terris YANG
Haiyou Wang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Honeywell International Inc
Original Assignee
Honeywell International Inc
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Filing date
Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Publication of EP4136064A1 publication Critical patent/EP4136064A1/en
Publication of EP4136064A4 publication Critical patent/EP4136064A4/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B01J19/004—Multifunctional apparatus for automatic manufacturing of various chemical products
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/18—Carbon
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/20—Carbon compounds
    • B01J27/22—Carbides
    • B01J27/224—Silicon carbide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
    • B01J29/035—Microporous crystalline materials not having base exchange properties, such as silica polymorphs, e.g. silicalites
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
    • C07C53/48—Halogenated acetyl halides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/00029—Batch processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002—Chemical plants
    • B01J2219/00027—Process aspects
    • B01J2219/00033—Continuous processes

Definitions

  • the present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst.
  • TFAI trifluoroacetyl iodide
  • TFAC trifluoroacetyl chloride
  • HI hydrogen iodide
  • Trifluoroiodomethane (CF 3 I) is an iodofluorocarbon (IFC).
  • IFCs consist mainly of carbon, fluorine, and iodine and have been identified as attractive potential replacements for chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs).
  • CFCs chlorofluorocarbons
  • HCFCs hydrochlorofluorocarbons
  • IFCs especially those containing just one iodine atom are non-flammable, have low boiling points, high volatilities, low viscosities, and low surface tensions, making them attractive alternative candidates as non-aqueous solvents for replacement of CFCs and HCFCs.
  • CF 3 I is non-flammable, has very low acute toxicity, extremely low Global Warming Potential (GWP) and negligible Ozone Depleting Potential (ODP).
  • GWP Global Warming Potential
  • ODP Ozone Depleting Potential
  • CF 3 I readily undergoes photolysis when exposed to UV radiation in the tropospheric layer of the atmosphere, and thus never reaches the stratosphere.
  • the short atmospheric life cycle of CF 3 I accounts for its extremely low GWP and negligible ODP.
  • CF 3 I is miscible with mineral oil and is also compatible with refrigeration system materials making it an acceptable environmentally benign candidate for applications in refrigeration, fire suppression, aerosol propellants, foam blowing, air conditioning, heat transfer media, and gaseous electrolytes.
  • HVAC Heating, Ventilation and Air Conditioning
  • R410A is a near azeotrope blend of difluoromethane (HFC-32) and pentafluoroethane (HFC-125) that is flammable, does not contribute to ozone depletion, and has high GWP.
  • a favorable process for making CF3I is to use trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) as starting materials to make the intermediate product trifluoroacetyl iodide (TFAI) which can be used to make CF3I in the next step reaction.
  • TFAC trifluoroacetyl chloride
  • HI hydrogen iodide
  • the present disclosure provides processes for producing trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) in liquid phase reaction with or without catalyst at ambient or elevated temperatures.
  • TFAI trifluoroacetyl iodide
  • TFAC trifluoroacetyl chloride
  • HI hydrogen iodide
  • the present disclosure provides a process for making trifluoroacetyl iodide (TFAI) in a liquid phase reaction.
  • TFAI trifluoroacetyl iodide
  • the present disclosure provides a liquid phase reaction of trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst, to form trifluoroacetyl iodide (TFAI).
  • the reaction may be performed at ambient or elevated temperatures.
  • the present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction comprising the steps of providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride and hydrogen iodide in a liquid phase reactor to produce trifluoroacetyl iodide.
  • TFAI trifluoroacetyl iodide
  • the mole ratio of trifluoroacetyl chloride to hydrogen iodide may be from about 1:10 to about 10:1.
  • the weight ratio of the catalyst to the trifluoroacetyl chloride may be from about 0.001:1 to about 0.5:1.
  • the catalyst may be selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
  • the liquid phase reaction of the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst may be conducted at a temperature from about 0°C to about 200°C.
  • the present disclosure further provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process comprising mixing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride, hydrogen iodide and an optional catalyst in a liquid phase reactor to produce trifluoroacetyl iodide and hydrogen chloride.
  • TFAI trifluoroacetyl iodide
  • the process may further include separating the trifluoroacetyl iodide from the hydrogen chloride.
  • the process provided by the present disclosure may be a continuous process.
  • the process provided by the present disclosure may be a batch process.
  • Fig. 1 corresponds to Example 1 and shows reactor pressure versus time for the liquid phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature.
  • TFAI trifluoroacetyl iodide
  • Fig. 2 corresponds to Example 2 and shows conversion of TFAC and selectivity for TFAI versus reaction time at ambient temperature.
  • Fig. 3 corresponds to Example 3 and shows conversion of TFAC and selectivity for TFAI versus reaction time at ambient temperature.
  • Fig. 4 corresponds to Example 4 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 90°C.
  • Fig. 5 corresponds to Example 5 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 90°C.
  • Fig. 6 corresponds to Example 6 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C.
  • Fig. 7 corresponds to Example 7 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C.
  • Fig. 8 corresponds to Example 8 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C.
  • Fig. 9 corresponds to Example 9 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 120°C.
  • Fig. 10 corresponds to Example 10 and shows conversion of TFAC and selectivity for both TFAI and CF3I versus reaction time at 120°C.
  • Fig. 11 corresponds to Example 11 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C in the presence of a catalyst.
  • Fig. 12 corresponds to Example 12 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C in the presence of a catalyst.
  • Fig. 13 corresponds to Example 13 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 90°C in the presence of a catalyst.
  • the present disclosure provides a liquid phase process for producing trifluoroacetyl iodide (TFAI) via the reaction shown below in Equation 1.
  • TFAI trifluoroacetyl iodide
  • Equation 1 CF3COCI + HI - CF3COI + HC1
  • the liquid phase process can be conducted in a liquid phase reactor with or without agitation.
  • the reactor is equipped with an agitator, and the reactor may be formed in whole or in part of materials including Hastelloy C 276, Inconel 600, Inconel 625, Monel 400, SS316, SS316L, PFA lined, PTFE lined, glass lined etc.
  • the reaction can be run under conditions effective to form trifluoroacetyl iodide (TFAI) but not CF 3 I to avoid the difficulties arising from the separation of trifluoroacetyl chloride (TFAC) from CF 3 I.
  • TFAI trifluoroacetyl iodide
  • TFAC trifluoroacetyl chloride
  • reaction temperatures may be as low as about 0°C, about 25°C, about 35°C, about 40°C, about 50°C, or as high as about 60°C, about 90°C, about 120°C, about 150°C, or about 200°C, or within any range defined between any two of the foregoing values.
  • the pressure may be as low as about 5 psig, about 25 psig, about 50 psig, about 100 psig, about 150 psig, about 200 psig, about 250 psig, or as high as about 300 psig, about 350 psig, about 400 psig, about 450 psig, about 500 psig, or within any range defined between any two of the foregoing values.
  • the TFAC:HI (trifluoroacetyl chloride:hydrogen iodide) ratio may be as low as about 1:10, about 2:1, about 3:1, about 4:1, or as high as about 5:1, about 6:1, about 7:1, about 8:1, about 9: 1, or about 10: 1, or within any range defined between any two of the foregoing values.
  • the TFAC:HI ratio is from 1 :2 to 2: 1, such as 1:1, 1:1.5, 1:1.9, 1.1:1, 1.5:1, 1.9:1, for example. More preferably, the TF AC/HI ratio is from 1:1 to 2:1.
  • a catalyst may be added to the reaction.
  • the catalyst may be silicon carbide, activated carbon, carbon molecular sieves, or combinations thereof.
  • the weight ratio of the catalyst to TFAC may be as low as about 0.001:1, about 0.01:1, about 0.02:1, about 0.03:1, about 0.04:1, or as high as about 0.05:1, about 0.06:1, about 0.07:1, about 0.08:1, about 0.09:1, about 0.1:1, about 0.2:1, about 0.5:1, or within any range defined between any two of the foregoing values.
  • the residence time may be as low as about 0.1 hour, about 0.5 hour, about 1 hour, about 5 hours, about 10 hours, about 15 hours, or as high as about 20 hours, about 30 hours, about 40 hours, about 50 hours, or within any range defined between any two of the foregoing values.
  • the reaction can be carried out in a batch-wise or continuous mode. Preferably, the reaction is carried out in a continuous mode.
  • the reactor may be equipped with a distillation column to remove low boiling by products, such as HC1. As reaction progresses, the TFAI concentration rises in the reactor and a liquid stream can be drawn continuously or intermittently for product separation.
  • the isolated TFAI can be sent to a storage tank for the use in next step reaction as raw material to make CF 3 I, while the separated TFAC and/or HI can be recycled back to the reactor.
  • TFAI trifluoroacetyl iodide
  • TFAI trifluoroacetyl iodide
  • TFAI trifluoroacetyl iodide
  • Aspect l is a process for producing trifluoroacetyl iodide (TFAI), the process comprising: providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and reacting the trifluoroacetyl chloride and hydrogen iodide to provide trifluoroacetyl iodide.
  • Aspect 2 is the process of Aspect 1, wherein in the providing step, the mole ratio of the trifluoroacetyl chloride to the hydrogen iodide is from about 1 : 10 to about 10:1.
  • Aspect 3 is the process of either of Aspect 1 or Aspect 2, wherein in the providing step, a weight ratio of the catalyst to the trifluoroacetyl chloride is from about 0.001 : 1 to about 0.5:1.
  • Aspect 4 is the process of any one of Aspects 1-3, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
  • Aspect 5 is the process of any one of Aspects 1-4, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 0°C to 200°C.
  • Aspect 6 is a process for producing trifluoroacetyl iodide (TFAI), the process comprising: mixing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and heating the trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst to produce trifluoroacetyl iodide and hydrogen chloride.
  • TFAI trifluoroacetyl iodide
  • Aspect 7 is the process of Aspect 6, further including separating the trifluoroacetyl iodide from the hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide.
  • Aspect 8 is the process of either of Aspect 6 or Aspect 7, wherein the process is a continuous process.
  • Aspect 9 is the process of either of Aspect 6 or Aspect 7, wherein the process is a batch process.
  • Aspect 10 is the process of any one of Aspects 6-9, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
  • Aspect 11 is the process of any one of Aspects 6-10, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 0°C to 200°C.
  • Aspect 12 is the process of any one of Aspects 6-11, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a pressure of 5 psig to 500 psig.

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Abstract

The present disclosure provides a process for making trifluoroacetyl iodide (TFAI) in a liquid phase reaction. Specifically, the present disclosure provides a liquid phase reaction of trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst, to form trifluoroacetyl iodide (TFAI). The reaction may be performed at ambient or elevated temperatures.

Description

SYNTHESIS OF TRIFLUOROACETYL IODIDE (TFAI) FROM TRIFLUORO ACETYL CHLORIDE (TFAC) AND HYDROGEN IODIDE (HI) IN A
LIQUID PHASE REACTION
CROSS-REFERENCE TO RELATED APPLICATION [0001] This application claims priority to U.S. Patent Application No. 17/219,390, filed March 31, 2021, which claims the benefit of U.S. Provisional Application No. 63/007,220, filed April 8, 2020, both of which are herein incorporated by reference in their entireties.
FIELD
[0002] The present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst.
BACKGROUND OF THE DISCLOSURE
[0003] Trifluoroiodomethane (CF3I) is an iodofluorocarbon (IFC). IFCs consist mainly of carbon, fluorine, and iodine and have been identified as attractive potential replacements for chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs). Broadly, IFCs, especially those containing just one iodine atom are non-flammable, have low boiling points, high volatilities, low viscosities, and low surface tensions, making them attractive alternative candidates as non-aqueous solvents for replacement of CFCs and HCFCs. Although iodine- containing organic compounds tend to be toxic, reactive, and chemically unstable the presence of the fluorine atoms bonded to the iodinated carbon atom offers considerable improvements in stability and greatly reduces toxicity. CF3I is non-flammable, has very low acute toxicity, extremely low Global Warming Potential (GWP) and negligible Ozone Depleting Potential (ODP). In addition, CF3I readily undergoes photolysis when exposed to UV radiation in the tropospheric layer of the atmosphere, and thus never reaches the stratosphere. The short atmospheric life cycle of CF3I accounts for its extremely low GWP and negligible ODP. Besides these properties, CF3I is miscible with mineral oil and is also compatible with refrigeration system materials making it an acceptable environmentally benign candidate for applications in refrigeration, fire suppression, aerosol propellants, foam blowing, air conditioning, heat transfer media, and gaseous electrolytes. [0004] With increasing mandates that require the phase down of high GWP products, an important objective of the Heating, Ventilation and Air Conditioning (HVAC) industry has been to develop a replacement for the industry standard refrigerant R410A. R410A is a near azeotrope blend of difluoromethane (HFC-32) and pentafluoroethane (HFC-125) that is flammable, does not contribute to ozone depletion, and has high GWP.
[0005] A favorable process for making CF3I is to use trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) as starting materials to make the intermediate product trifluoroacetyl iodide (TFAI) which can be used to make CF3I in the next step reaction.
[0006] The present disclosure provides processes for producing trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI) in liquid phase reaction with or without catalyst at ambient or elevated temperatures.
SUMMARY
[0007] The present disclosure provides a process for making trifluoroacetyl iodide (TFAI) in a liquid phase reaction. Specifically, the present disclosure provides a liquid phase reaction of trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), with or without a catalyst, to form trifluoroacetyl iodide (TFAI). The reaction may be performed at ambient or elevated temperatures.
[0008] The present disclosure provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction comprising the steps of providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride and hydrogen iodide in a liquid phase reactor to produce trifluoroacetyl iodide.
[0009] The mole ratio of trifluoroacetyl chloride to hydrogen iodide may be from about 1:10 to about 10:1.
[0010] The weight ratio of the catalyst to the trifluoroacetyl chloride may be from about 0.001:1 to about 0.5:1.
[0011] The catalyst may be selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
[0012] The liquid phase reaction of the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst may be conducted at a temperature from about 0°C to about 200°C.
[0013] The present disclosure further provides a process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process comprising mixing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst, and reacting the trifluoroacetyl chloride, hydrogen iodide and an optional catalyst in a liquid phase reactor to produce trifluoroacetyl iodide and hydrogen chloride.
[0014] The process may further include separating the trifluoroacetyl iodide from the hydrogen chloride.
[0015] The process provided by the present disclosure may be a continuous process.
[0016] The process provided by the present disclosure may be a batch process.
DESCRIPTION OF THE DRAWINGS [0017] Fig. 1 corresponds to Example 1 and shows reactor pressure versus time for the liquid phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature.
[0018] Fig. 2 corresponds to Example 2 and shows conversion of TFAC and selectivity for TFAI versus reaction time at ambient temperature.
[0019] Fig. 3 corresponds to Example 3 and shows conversion of TFAC and selectivity for TFAI versus reaction time at ambient temperature.
[0020] Fig. 4 corresponds to Example 4 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 90°C.
[0021] Fig. 5 corresponds to Example 5 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 90°C. [0022] Fig. 6 corresponds to Example 6 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C.
[0023] Fig. 7 corresponds to Example 7 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C.
[0024] Fig. 8 corresponds to Example 8 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C.
[0025] Fig. 9 corresponds to Example 9 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 120°C.
[0026] Fig. 10 corresponds to Example 10 and shows conversion of TFAC and selectivity for both TFAI and CF3I versus reaction time at 120°C. [0027] Fig. 11 corresponds to Example 11 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C in the presence of a catalyst.
[0028] Fig. 12 corresponds to Example 12 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 60°C in the presence of a catalyst. [0029] Fig. 13 corresponds to Example 13 and shows conversion of TFAC and selectivity for TFAI versus reaction time at 90°C in the presence of a catalyst.
DETAILED DESCRIPTION
[0030] The present disclosure provides a liquid phase process for producing trifluoroacetyl iodide (TFAI) via the reaction shown below in Equation 1.
Equation 1 : CF3COCI + HI - CF3COI + HC1
[0031] The liquid phase process can be conducted in a liquid phase reactor with or without agitation. Preferably, the reactor is equipped with an agitator, and the reactor may be formed in whole or in part of materials including Hastelloy C 276, Inconel 600, Inconel 625, Monel 400, SS316, SS316L, PFA lined, PTFE lined, glass lined etc.
[0032] The reaction can be run under conditions effective to form trifluoroacetyl iodide (TFAI) but not CF3I to avoid the difficulties arising from the separation of trifluoroacetyl chloride (TFAC) from CF3I.
[0033] The reaction temperatures may be as low as about 0°C, about 25°C, about 35°C, about 40°C, about 50°C, or as high as about 60°C, about 90°C, about 120°C, about 150°C, or about 200°C, or within any range defined between any two of the foregoing values.
[0034] The pressure may be as low as about 5 psig, about 25 psig, about 50 psig, about 100 psig, about 150 psig, about 200 psig, about 250 psig, or as high as about 300 psig, about 350 psig, about 400 psig, about 450 psig, about 500 psig, or within any range defined between any two of the foregoing values.
[0035] The TFAC:HI (trifluoroacetyl chloride:hydrogen iodide) ratio may be as low as about 1:10, about 2:1, about 3:1, about 4:1, or as high as about 5:1, about 6:1, about 7:1, about 8:1, about 9: 1, or about 10: 1, or within any range defined between any two of the foregoing values. Preferably, the TFAC:HI ratio is from 1 :2 to 2: 1, such as 1:1, 1:1.5, 1:1.9, 1.1:1, 1.5:1, 1.9:1, for example. More preferably, the TF AC/HI ratio is from 1:1 to 2:1. [0036] A catalyst may be added to the reaction. The catalyst may be silicon carbide, activated carbon, carbon molecular sieves, or combinations thereof. The weight ratio of the catalyst to TFAC may be as low as about 0.001:1, about 0.01:1, about 0.02:1, about 0.03:1, about 0.04:1, or as high as about 0.05:1, about 0.06:1, about 0.07:1, about 0.08:1, about 0.09:1, about 0.1:1, about 0.2:1, about 0.5:1, or within any range defined between any two of the foregoing values.
[0037] The residence time may be as low as about 0.1 hour, about 0.5 hour, about 1 hour, about 5 hours, about 10 hours, about 15 hours, or as high as about 20 hours, about 30 hours, about 40 hours, about 50 hours, or within any range defined between any two of the foregoing values.
[0038] The reaction can be carried out in a batch-wise or continuous mode. Preferably, the reaction is carried out in a continuous mode.
[0039] The reactor may be equipped with a distillation column to remove low boiling by products, such as HC1. As reaction progresses, the TFAI concentration rises in the reactor and a liquid stream can be drawn continuously or intermittently for product separation.
The isolated TFAI can be sent to a storage tank for the use in next step reaction as raw material to make CF3I, while the separated TFAC and/or HI can be recycled back to the reactor.
EXAMPLES
[0040] In the following examples, the manufacture of TFAI from TFAC and HI in a liquid phase process is demonstrated.
Example 1
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature [0041] At ambient temperature, 19.94 grams of HI and 22.97 grams of TFAC (TF AC/HI molar ratio of 1.11 : 1.00) were charged into a 100 mL 316L reactor equipped with a pressure gauge without agitation. The cylinder pressure was monitored to track the progress of the reaction with the pressure profile as shown in Fig. 1. After 5.3 hours, the reactor pressure was stabilized at 168 psig. After 17.5 hours, the reactor was drained and the liquid sample was analyzed by gas chromatography (GC). The results show 76.04 % conversion of TFAC, and 99.99 % selectivity for TFAI. No CF3I formation was observed.
Example 2
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature [0042] At ambient temperature, 19.48 grams of HI and 21.21 grams of TFAC (TF AC/HI molar ratio of 1.05 : 1.00) were charged into a 100 mL 316L reactor equipped with a pressure gauge without agitation. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 2. The results show that, during the first 12 hours, TFAC conversion was increased with increasing reaction time, reaching about 85.4% after 14 hours. Near 100% selectivity for TFAI was observed throughout the entire run. No CF3I formation was observed.
Example 3
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at ambient temperature
[0043] At ambient temperature, 47.71 grams of HI and 70.30 grams of TFAC (TF AC/HI molar ratio of 1.42: 1.00) were charged into a 300 mL Teflon-lined PARR reactor equipped with an agitator. The reactor was agitated during the test period. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 3. After 14 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 65-66% conversion of TFAC and >99.9% selectivity for TFAI. No CF3I formation was observed.
Example 4
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 90°C
[0044] A 300 mL Teflon-lined PARR reactor equipped with an agitator was charged with 64.33 grams of TFAC. The reactor was agitated and heated to 70°C, then 56.67 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.10: 1.00). The reactor temperature controller was set at 90°C, with peak temperature of 98°C observed due to exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 4. After 4 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed about 84% conversion of TFAC and >99.9% selectivity for TFAI. No CF3I formation was observed. Example 5
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 90°C
[0045] A 300 mL Teflon-lined PARR reactor equipped with an agitator was charged with 65.49 grams of TFAC. The reactor was agitated and heated to 70°C, then 51.08 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.24: 1.00). The reactor temperature controller was set at 90°C, with peak temperature of 97.7°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 5. After 6 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 77-78% conversion of TFAC and >99.9% selectivity for TFAI. No CF3I formation was observed.
Example 6
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 60°C
[0046] A 300 mL Teflon-lined PARR reactor with agitator was charged with 70.63 grams of TFAC. The reactor was agitated and heated to 35°C, then 61.34 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.11 : 1.00). The reactor temperature controller was set at 60°C, with peak temperature of 61.5°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 6. After 6 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed roughly 85% conversion of TFAC and >99.9% selectivity for TFAI. No CF3I formation was observed.
Example 7
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 60°C
[0047] A 300 mL Teflon-lined PARR reactor equipped with an agitator was charged with 74.18 grams of TFAC. The reactor was agitated and heated to 35°C, then 42.58 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.68: 1.00). The reactor temperature controller was set at 60°C, with peak temperature of 65°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 7. After 10.5 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis from the final liquid sample showed roughly 60% conversion of TFAC and near 100% selectivity for TFAT No CF3I formation was observed.
Example 8
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 60°C
[0048] A 300 mL Teflon-lined PARR reactor equipped with an agitator was charged with 75.10 grams of TFAC. The reactor was agitated and heated up 35°C, then 38.77 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.87: 1.00). The reactor temperature controller was set at 60°C, with peak temperature of 66.3°C observed due to exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity shown in Fig. 8. After 6 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 51-52% conversion of TFAC and near 100% selectivity for TFAI. No CF3I formation was observed.
Example 9
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 120°C
[0049] A 300 mL Teflon-lined PARR reactor equipped with an agitator was charged with 65.60 grams of TFAC. The reactor was agitated and heated to 85°C, then 56.12 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.13 : 1.00). The reactor temperature controller was set at 120°C, with peak temperature of 121.3°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 9. After 5 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 80-81% conversion of TFAC, 99.79% selectivity for TFAI, and 0.10% selectivity for CF3I. Example 10
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 120°C
[0050] A 300 mL Teflon-lined PARR reactor equipped with an agitator was charged with 61.08 grams of TFAC. The reactor was agitated and heated up 85°C, then 40.99 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.44: 1.00). The reactor temperature controller was set at 120°C, with peak temperature of 120.9°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity as shown in Fig. 10. After 3 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 72-73% conversion of TFAC, 99.82% selectivity for TFAI, and 0.13% selectivity for CF3I.
Example 11
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) with catalyst
[0051] 1.13 grams of silicon carbide (SiC) catalyst and 71.44 grams of TFAC were charged into a 300 mL Teflon-lined PARR reactor equipped with an agitator. The weight ratio of the catalyst to the TFAC was 0.016: 1.00. The reactor was agitated and heated to 35°C, then 65.39 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.05 : 1.00). The reactor temperature controller was set at 60°C, with peak temperature of 60.2°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity shown in Fig. 11. After 5 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 85-86% conversion of TFAC and 99.9% selectivity for TFAI. No CF3I formation was observed.
Example 12
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) with catalyst
[0052] 1.09 grams of silicon carbide (SiC) catalyst, and 74.95 grams of TFAC were charged into a 300 mL Teflon-lined PARR reactor equipped with an agitator. The weight ratio of the catalyst to the TFAC was 0.014: 1.00. The reactor was agitated and heated to 35°C, then 53.80 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.35:1.00). The reactor temperature controller was set at 60°C, with peak temperature of 60.9°C observed due to the exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity shown in Fig. 12. After 5 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 72-73% conversion of TFAC and >99.9% selectivity for TFAI. No CF3I formation was observed.
Example 13
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) with catalyst
[0053] 1.10 grams of silicon carbide (SiC) catalyst, and 76.26 grams of TFAC were charged into a 300 mL Teflon-lined PARR reactor equipped with an agitator. The weight ratio of the catalyst to the TFAC was 0.014: 1.00. The reactor was agitated and heated to 75°C, then 57.12 grams of HI was charged into the reactor (TF AC/HI molar ratio of 1.29: 1.00). The reactor temperature controller was set at 90°C, with peak temperature of 107.3°C observed due to exothermic reaction. Periodically, a small amount of liquid sample was drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity shown in Fig. 13. After 6 hours, the reactor was drained, and the liquid samples were analyzed by GC. The analysis of the final liquid sample showed 74-75% conversion of TFAC and >99.9% selectivity for TFAI. No CF3I formation was observed.
Example 14
Liquid phase synthesis of trifluoroacetyl iodide (TFAI)
[0054] Hydrogen iodide (172.7 grams) and 20.0 grams of TFAC (TF AC/HI molar ratio of 1.0:9.0) are charged into a 100 mL 316L reactor equipped with a pressure gauge without agitation. Periodically, a small amount of liquid sample is drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity. After a time, the reactor is drained, and the liquid samples are analyzed by GC. Example 15
Liquid phase synthesis of trifluoroacetyl iodide (TFAI)
[0055] Hydrogen iodide (20.0 grams) and 165.6 grams of TFAC (TF AC/HI molar ratio of 8.0: 1.0) are charged into a 100 mL 316L reactor equipped with a pressure gauge without agitation. Periodically, a small amount of liquid sample is drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity. After a time, the reactor is drained, and the liquid samples are analyzed by GC.
Example 16
Liquid phase synthesis of trifluoroacetyl iodide (TFAI) at 200°C [0056] A 300 mL Teflon-lined PARR reactor equipped with an agitator is charged with 61.08 grams of TFAC. The reactor is agitated and heated up to 180°C, then 40.99 grams of HI is charged into the reactor (TF AC/HI molar ratio of 1.44: 1.00). The reactor temperature controller is set at 200°C. Periodically, a small amount of liquid sample is drained and analyzed by gas chromatography (GC) to track the progress of the reaction with the TFAC conversion and TFAI selectivity. After a time, the reactor is drained, and the liquid samples are analyzed by GC.
[0057] It should be understood that the foregoing description is only illustrative of the present disclosure. Various alternatives and modifications can be devised by those skilled in the art without departing from the disclosure. Accordingly, the present disclosure is intended to embrace all such alternatives, modifications and variances that fall within the scope of the appended claims.
ASPECTS
[0058] Aspect l is a process for producing trifluoroacetyl iodide (TFAI), the process comprising: providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and reacting the trifluoroacetyl chloride and hydrogen iodide to provide trifluoroacetyl iodide. [0059] Aspect 2 is the process of Aspect 1, wherein in the providing step, the mole ratio of the trifluoroacetyl chloride to the hydrogen iodide is from about 1 : 10 to about 10:1.
[0060] Aspect 3 is the process of either of Aspect 1 or Aspect 2, wherein in the providing step, a weight ratio of the catalyst to the trifluoroacetyl chloride is from about 0.001 : 1 to about 0.5:1. [0061] Aspect 4 is the process of any one of Aspects 1-3, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
[0062] Aspect 5 is the process of any one of Aspects 1-4, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 0°C to 200°C.
[0063] Aspect 6 is a process for producing trifluoroacetyl iodide (TFAI), the process comprising: mixing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and heating the trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst to produce trifluoroacetyl iodide and hydrogen chloride.
[0064] Aspect 7 is the process of Aspect 6, further including separating the trifluoroacetyl iodide from the hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide.
[0065] Aspect 8 is the process of either of Aspect 6 or Aspect 7, wherein the process is a continuous process. [0066] Aspect 9 is the process of either of Aspect 6 or Aspect 7, wherein the process is a batch process.
[0067] Aspect 10 is the process of any one of Aspects 6-9, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof. [0068] Aspect 11 is the process of any one of Aspects 6-10, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 0°C to 200°C.
[0069] Aspect 12 is the process of any one of Aspects 6-11, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a pressure of 5 psig to 500 psig.

Claims

1. A process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process comprising: providing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; reacting the trifluoroacetyl chloride and hydrogen iodide to provide trifluoroacetyl iodide.
2. The process of claim 1, wherein in the providing step, the mole ratio of the trifluoroacetyl chloride to the hydrogen iodide is from about 1 : 10 to about 10:1.
3. The process of either claim 1 or claim 2, wherein in the providing step, a weight ratio of the catalyst to the trifluoroacetyl chloride may be from about 0.001:1 to about 0.5:1.
4. The process of any one of claims 1-3, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
5. A process for producing trifluoroacetyl iodide (TFAI) in a liquid phase reaction, the process comprising: mixing trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst; and heating the trifluoroacetyl chloride, hydrogen iodide, and an optional catalyst to produce trifluoroacetyl iodide and hydrogen chloride.
6. The process of claim 5, further including separating the trifluoroacetyl iodide from the hydrogen chloride, trifluoroacetyl chloride, and hydrogen iodide.
7. The process of either claim 5 or claim 6, wherein the process is one of a continuous process and a batch process.
8. The process of any one of claims 5-7, wherein the catalyst is selected from the group consisting of silicon carbide, activated carbon, carbon molecular sieves, and combinations thereof.
9. The process of any one of claims 5-8, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a temperature from 0°C to 200°C.
10. The process of any one of claims 5-9, wherein in the reacting step, the trifluoroacetyl chloride, the hydrogen iodide, and the optional catalyst are at a pressure of 5 psig to 500 psig.
EP21784224.4A 2020-04-08 2021-04-06 SYNTHESIS OF TRIFLUOROACETYL IODIDE (TFAI) FROM TRIFLUOROACETYL CHLORIDE (TFAC) AND HYDROGEN IODIDE (HI) IN A LIQUID PHASE REACTION Pending EP4136064A4 (en)

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PCT/US2021/025961 WO2021207194A1 (en) 2020-04-08 2021-04-06 Synthesis of trifluoroacetyl iodide (tfai) from trifluoroacetyl chloride (tfac) and hydrogen iodide (hi) in a liquid phase reaction

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